Dimethylformamide → HCID 67065123, compound

HRID 546967Notes

Reaction equation

[CH2:1]([C:3]([C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]2([OH:36])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[C:24]([CH3:37])[CH:23]=1)([C:6]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[C:8]([CH3:21])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].[CH3:38][O:39][C:40](=[O:49])[CH2:41][C:42]1[CH:43]=[N:44][CH:45]=[C:46](Br)[CH:47]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:58]N(C)C=O>>[CH2:38]([O:39][C:40](=[O:49])[CH2:41][C:42]1[CH:43]=[N:44][CH:45]=[C:46]([C:9]2[CH:10]=[CH:11][C:6]([C:3]([CH2:4][CH3:5])([C:22]3[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]4([OH:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]4)=[C:24]([CH3:37])[CH:23]=3)[CH2:1][CH3:2])=[CH:7][C:8]=2[CH3:21])[CH:47]=1)[CH3:58]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 62657Potassium Phosphate, Tribasic

HCID 23398394Methyl 2-(5-bromopyridin-3-yl)acetate

HCID 57463792HCID 57463792, compound

Product 1

HCID 67065123HCID 67065123, compoundYield 91%

Conditions

Temperature: 140 °C

Procedure

A solution of 1-[(E)-2-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-vinyl]-cyclohexanol (Example 36-(3); 0.05 g, 0.0994 mmol), (5-bromo-pyridin-3-yl)acetic acid methyl ester (Example 24-(2); 34.3 mg, 0.14 mmol), tetrakistriphenylphosphine palladium (16.0 mg, 0.0139 mmol) and potassium phosphate (31.7 mg, 0.14 mmol) in N,N-dimethylformamide (0.27 mL) was stirred with microwave heating at 140° C. for 10 minutes. The reaction mixture was filtered through cotton plug, and the mixture was purified by silica gel chromatography (40% ethyl acetate/hexane) to give the title compound (47.8 mg, 91%).

Workup

filtrationThe reaction mixture was filtered through cotton plug
customthe mixture was purified by silica gel chromatography (40% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-fd70e18f20104bd99df94c2fcece9855
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935688B2

Reaction notes

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