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Dichloromethane → (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(2-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridine-4-yl)benzo[d]thiazol-6-yl)acetate

HRID 879384
Notes
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Reaction equation

HRID 879384 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([CH3:11])[NH:8][C:5]2=[N:6][CH:7]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.ClCCl.C([O-])(=O)C.[K+].[C:38]([O:42][C@@H:43]([C:49]1[C:64]([CH3:65])=[CH:63][C:52]2[N:53]=[C:54]([C:56]3[CH:61]=[CH:60][N:59]=[C:58](Cl)[CH:57]=3)[S:55][C:51]=2[C:50]=1[C:66]1[CH:71]=[CH:70][C:69]([Cl:72])=[CH:68][CH:67]=1)[C:44]([O:46][CH2:47][CH3:48])=[O:45])([CH3:41])([CH3:40])[CH3:39].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[C:38]([O:42][C@@H:43]([C:49]1[C:64]([CH3:65])=[CH:63][C:52]2[N:53]=[C:54]([C:56]3[CH:61]=[CH:60][N:59]=[C:58]([C:2]4[CH:3]=[C:4]5[CH:10]=[C:9]([CH3:11])[NH:8][C:5]5=[N:6][CH:7]=4)[CH:57]=3)[S:55][C:51]=2[C:50]=1[C:66]1[CH:67]=[CH:68][C:69]([Cl:72])=[CH:70][CH:71]=1)[C:44]([O:46][CH2:47][CH3:48])=[O:45])([CH3:39])([CH3:40])[CH3:41]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 6

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 454896915-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridineHCID 86700142(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

Product 1

HCID 86700193(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(2-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridine-4-yl)benzo[d]thiazol-6-yl)acetate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine (60 mg, 0.284 mmol) in dioxane (3 mL) was added bis(pinacolato)diboron (87 mg, 0.341 mmol), [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (23 mg, 0.028 mmol), potassium acetate (84 mg, 0.852 mmol). The mixture was degassed and heated at 100° C. for 2 h. The mixture was cooled, and then added (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (100 mg, 0.189 mmol), tetrakis(triphenylphosphine)palladium(0) (22 mg, 0.019 mmol), K2CO3 (131 mg, 0.948 mmol) and water (1 mL, degassed). The reaction mixture was heated at 110° C. for 1 h, cooled and partitioned between ethyl acetate and brine. The organic layer was separated, dried over Na2SO4 and concentrated to give crude which was purified by chromatographic column to afford the desired product. LCMS-ESI+: calc'd for C35H33ClN4O3S: 625.2 (M+H+); Found: 625.3 (M+H+).

Workup

  1. customThe mixture was degassed
  2. temperatureThe mixture was cooled
  3. temperatureThe reaction mixture was heated at 110° C. for 1 h
  4. temperaturecooled
  5. custompartitioned between ethyl acetate and brine
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customto give crude which
  10. customwas purified by chromatographic column

Sources & evidence

ORD record
ord-78ea7fcce26f444c887371ac584749c7
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08987250B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes