Potassium Carbonate → HCID 70980960, compound

HRID 1468694Notes

Reaction equation

HRID 1468694 reaction equation
[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:26]([CH3:27])=[CH:25][C:18]2[N:19]=[C:20]([CH:22]3[CH2:24][CH2:23]3)[S:21][C:17]=2[C:16]=1Br)[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[O:29]1[C:40]2[C:41]3[C:36]([C:37](B(O)O)=[CH:38][CH:39]=2)=[N:35][CH:34]=[CH:33][C:32]=3[CH2:31][CH2:30]1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O.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>[C:1]([O:7][CH2:8][C@@H:9]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:15]1[C:26]([CH3:27])=[CH:25][C:18]2[N:19]=[C:20]([CH:22]3[CH2:24][CH2:23]3)[S:21][C:17]=2[C:16]=1[C:37]1[C:36]2[C:41]3=[C:32]([CH2:31][CH2:30][O:29][C:40]3=[CH:39][CH:38]=1)[CH:33]=[CH:34][N:35]=2)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 59578523HCID 59578523, compoundHCID 70981621HCID 70981621, compound

Product 1

HCID 70980960HCID 70980960, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31374DimethylacetamideSolvent

Procedure

To a solution of (S)-2-(7-bromo-2-cyclopropyl-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate (18) (23 mg, 0.047 mmol) in DMA (2 ml), was added 2,3-dihydropyrano[4,3,2-de]quinolin-7-ylboronic acid (25 mg, 0.099 mmol), 2N K2CO3 solution (0.11 ml, 0.22 mmol) and Pd(PPh3)4 (6 mg, 0.005 mmol). The reaction mixture was reacted at 85° C. for 2 hs. The reaction was cooled down, washed by saturated NaHCO3 solution, extracted by EtOAc. The organic phase was combined, dry over MgSO4, filtered, concentrated and purified by silica gel column, eluting by 0-50% EtOAc in hexanes. Two isomers were separated and went through the chemistry sequence as above. LCMS-ESI+: calc'd for C33H38N2O4S: 559.2 (M+H+). Found: 559.1 (M+H+).

Workup

  1. customThe reaction mixture was reacted at 85° C. for 2 hs
  2. temperatureThe reaction was cooled down
  3. washwashed by saturated NaHCO3 solution
  4. extractionextracted by EtOAc
  5. dry with materialdry over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel column
  9. washeluting by 0-50% EtOAc in hexanes
  10. customTwo isomers were separated

Sources & evidence

ORD record
ord-fc54f258afe5475a87923796414271bb
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

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