Potassium Phosphate, Tribasic → HCID 25096663, compound

HRID 1926949Notes

Reaction equation

P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:9][O:10][C:11](=[O:36])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]1[C:19]2[C:26]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)=[C:25](Br)[O:24][C:20]=2[N:21]=[CH:22][N:23]=1.[Cl:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1B1OC(C)(C)C(C)(C)O1>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:9][O:10][C:11](=[O:36])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]1[C:19]2[C:26]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)=[C:25]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=3[Cl:37])[O:24][C:20]=2[N:21]=[CH:22][N:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Add 229 mg (1.08 mmol) potassium phosphate to a mixture of 220 mg (0.49 mmol) 6-{[6-bromo-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoic acid methyl ester and 17 mg (0.03 mmol) bis(triphenylphosphine)palladium(II) chloride in 2.2 ml toluene. Next, add 176 mg (0.74 mmol) (2-chlorophenyl)boronic acid pinacol ester and stir the mixture for 15 h at 80° C. Purify the reaction mixture directly by preparative RP-HPLC (gradient: water/acetonitrile). 101 mg (42% of theor.) of the desired product is obtained.

Workup

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

Sources & evidence

ORD record: ord-d5a6426d797b497dac0f09ab2ff88c9c
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183246B2

Reaction notes

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