Methanol → HCID 58280144, compound

HRID 2189119Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].CO.[CH2:9]([C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1)[CH3:10].[CH3:20][O:21][C:22](=[O:49])[CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][CH2:29][C@H:28]([O:32][C:33]2[C:34]3[C:41](Br)=[C:40]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[O:39][C:35]=3[N:36]=[CH:37][N:38]=2)[CH2:27]1>CS(C)=O.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>[CH3:20][O:21][C:22](=[O:49])[CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][CH2:29][C@H:28]([O:32][C:33]2[C:34]3[C:41]([C:14]4[CH:15]=[CH:16][C:11]([CH2:9][CH3:10])=[CH:12][CH:13]=4)=[C:40]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[O:39][C:35]=3[N:36]=[CH:37][N:38]=2)[CH2:27]1

Participants

Conditions

Temperature: 80 °C

Procedure

Add 5.2 mg (0.007 mmol) of bis(triphenylphosphine)palladium(II) chloride,. 30.6 mg (0.221 mmol) of potassium carbonate, 0.04 ml of methanol and 31 mg (0.207 mmol) of 4-ethylbenzeneboronic acid successively under argon to a solution of 70 mg (0.148 mmol) of (+)-4-{(3S)-3-[(5-bromo-6-phenylfuro[2,3-d]pyrimidin-4-yl)oxy]piperidin-1-yl}butanoic acid methyl ester in 0.4 ml of DMSO. Stir the mixture at 80° C. for a total of 3.5 h. After cooling, purify the reaction mixture directly by preparative RP-HPLC (eluent: acetonitrile/water gradient). 37.3 mg (50.6% of theory) of the target compound are isolated.

Workup

temperatureAfter cooling
custompurify the reaction mixture directly by preparative RP-HPLC (eluent: acetonitrile/water gradient)
custom37.3 mg (50.6% of theory) of the target compound are isolated

Sources & evidence

ORD record: ord-1d6fc32abe3b4f4eb05495a6dbdc8606
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324222B2

Reaction notes

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