Potassium Phosphate, Tribasic → HCID 57709081, compound

HRID 546980Notes

Reaction equation

[CH2:1]([C:3]([C:26]1[CH:31]=[CH:30][C:29](B2OC(C)(C)C(C)(C)O2)=[C:28]([CH3:41])[CH:27]=1)([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2([O:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:8]([CH3:25])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].[CH3:42][O:43][C:44](=[O:53])[CH2:45][C:46]1[CH:47]=[N:48][CH:49]=[C:50](Br)[CH:51]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O>[CH3:42][O:43][C:44](=[O:53])[CH2:45][C:46]1[CH:47]=[N:48][CH:49]=[C:50]([C:29]2[CH:30]=[CH:31][C:26]([C:3]([CH2:4][CH3:5])([C:6]3[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]4([O:20][Si:21]([CH3:23])([CH3:24])[CH3:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]4)=[C:8]([CH3:25])[CH:7]=3)[CH2:1][CH3:2])=[CH:27][C:28]=2[CH3:41])[CH:51]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A solution of 2-(4-{1-ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclohexylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Example 35-(4); 57.6 mg, 0.10 mmol), (5-bromo-pyridin-3-yl)acetic acid methyl ester (Example 24-(2); 30.1 mg, 0.13 mmol), tetrakistriphenylphosphine palladium (14.1 mg, 0.0122 mmol) and potassium phosphate (27.8 mg, 0.13 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 (45% ethyl acetate/hexane) to give the title compound (37.3 mg, 62%).

Workup

filtrationThe reaction mixture was filtered through cotton plug
customthe mixture was purified by silica gel chromatography (45% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-8486a02995cf49fd9a8cb4a4ecc0fb31
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935688B2

Reaction notes

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