Sodium Carbonate → HCID 58052307, compound

HRID 2190210Notes

Reaction equation

HRID 2190210 reaction equation
CO[C:3]1C=CC=C(OC)[C:8]=1[C:9]1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[OH:30][CH:31]([CH2:40][CH2:41][CH2:42][N:43]([C:48]1[N:53]=[C:52]2[O:54][C:55]([C:61]3[CH:66]=[CH:65][C:64]([CH3:67])=[CH:63][CH:62]=3)=[C:56]([C:57](=[O:60])[NH:58][CH3:59])[C:51]2=[CH:50][C:49]=1I)[S:44]([CH3:47])(=[O:46])=[O:45])[C:32]([CH3:39])([CH3:38])[C:33]([O:35][CH2:36][CH3:37])=[O:34].B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.O.CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[CH2:36]([O:35][C:33](=[O:34])[C:32]([CH3:38])([CH3:39])[CH:31]([OH:30])[CH2:40][CH2:41][CH2:42][N:43]([C:48]1[N:53]=[C:52]2[O:54][C:55]([C:61]3[CH:66]=[CH:65][C:64]([CH3:67])=[CH:63][CH:62]=3)=[C:56]([C:57](=[O:60])[NH:58][CH3:59])[C:51]2=[CH:50][C:49]=1[CH:9]1[CH2:8][CH2:3]1)[S:44]([CH3:47])(=[O:45])=[O:46])[CH3:37]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 61668Boronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 58052327HCID 58052327, compound

Product 1

HCID 58052307HCID 58052307, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of S-Phos (0.4 eq., 15 mg), Pd(OAc)2 (0.2 eq., 4.0 mg) and PhMe (3 ml) was added ethyl 3-hydroxy-6-(N-(5-iodo-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6-yl)methylsulfonamido)-2,2-dimethylhexanoate (1 eq., 60 mg). A solution of boronic acid (30 eq., 232 mg) and Na2CO3 (2 N aqueous solution, 40 eq., 0.54 ml) was added. The mixture was heated in a sealed tube under nitrogen at 115° C. for 60 min, cooled, and diluted with DCM and water. The aqueous layer was extracted with DCM. Orgnic layers were washed with saturated aqueous Na2CO3 solution and concentrated to yield the crude title compound which was used in next step without purification.

Workup

  1. temperaturecooled
  2. extractionThe aqueous layer was extracted with DCM
  3. washOrgnic layers were washed with saturated aqueous Na2CO3 solution
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-be8e62b47d264c1f986aeefa007b3870
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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