3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-1-ol → HCID 178485573, compound

HRID 2279902Notes

Reaction equation

HRID 2279902 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:11])[NH:9][CH3:10])[C:5]([NH:12][C:13]2[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15]([NH:23][C:24]3[CH:35]=[CH:34][C:27]([CH2:28][CH2:29][CH2:30][PH:31](=[O:33])[OH:32])=[CH:26][C:25]=3[O:36][CH3:37])[N:14]=2)=[CH:4][CH:3]=1.[CH3:38][C:39]1([CH3:55])[C:43]([CH3:45])([CH3:44])[O:42][B:41]([C:46]2[CH:47]=[N:48][N:49]([CH2:51][CH2:52][CH2:53]O)[CH:50]=2)[O:40]1>>[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:11])[NH:9][CH3:10])[C:5]([NH:12][C:13]2[C:18]([C:19]([F:22])([F:20])[F:21])=[CH:17][N:16]=[C:15]([NH:23][C:24]3[CH:35]=[CH:34][C:27]([CH2:28][CH2:29][CH2:30][PH:31](=[O:32])[O:33][CH2:53][CH2:52][CH2:51][N:49]4[CH:50]=[C:46]([B:41]5[O:42][C:43]([CH3:45])([CH3:44])[C:39]([CH3:38])([CH3:55])[O:40]5)[CH:47]=[N:48]4)=[CH:26][C:25]=3[O:36][CH3:37])[N:14]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 671871273-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-1-ol2×HCID 178485570HCID 178485570, compound2×

Product 1

HCID 178485573HCID 178485573, compoundYield 90.2%

Procedure

This material was prepared analogously to Example 44A using (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)ethylphosphinic acid (Compound 67B, 0.220 g, 0.365 mmol) and 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-1-ol (Compound 3E, 0.0918 g, 0.364 mmol) to afford the title compound as an off-white foam (275 mg, 90%). MS (ESI): m/z 837.21/839.20 [M+H]+. UPLC: tR=1.14 min (UPLC-TOF: polar—2 min).

Workup

  1. customThis material was prepared analogously to Example 44A

Sources & evidence

ORD record
ord-9dd1047fd78846c18282e4a04900e08f
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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