Sodium Carbonate → HCID 25096664, compound

HRID 1926950Notes

Reaction equation

HRID 1926950 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[C:17](Br)[O:16][C:12]=2[N:13]=[CH:14][N:15]=1.[F:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:31]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[C:17]([C:31]3[C:30]([F:29])=[CH:35][CH:34]=[CH:33][C:32]=3[F:36])[O:16][C:12]=2[N:13]=[CH:14][N:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343362,6-Difluorophenylboronic acidHCID 58016901Methyl 6-{[6-bromo-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoate

Product 1

HCID 25096664HCID 25096664, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Dissolve 150 mg (0.34 mmol) 6-{[6-bromo-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoic acid methyl ester and 106 mg (0.70 mmol) (2,6-difluorophenyl)boronic acid in 3.5 ml toluene and 1.0 ml ethanol, and add 0.34 ml of 2 M aqueous sodium carbonate solution and 25 mg (0.03 mmol) 1,1′-bis(diphenylphosphano)ferrocene palladium(II) chloride. Next, stir for 15 h at 70° C. Purify the reaction mixture directly by preparative RP-HPLC (gradient: water/acetonitrile). 13 mg (8% of theor.) of the desired product is obtained.

Workup

  1. customPurify the reaction mixture directly by preparative RP-HPLC (gradient: water/acetonitrile)

Sources & evidence

ORD record
ord-55d624e9d08d4977a48a9e27cade187d
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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