4-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-indole-2-carboxamide → HCID 178487949, compound

HRID 245672Notes

Reaction equation

HRID 245672 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([CH3:20])[C:14]3=[C:13](Br)[N:12]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[CH3:22][O:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:25]=1[CH:26]=[C:27]([C:34]([NH:36][C:37]1[CH:42]=[CH:41][C:40](B3OC(C)(C)C(C)(C)O3)=[CH:39][C:38]=1[O:52][CH3:53])=[O:35])[N:28]2[CH3:33]>>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([CH3:20])[C:14]3=[C:13]([C:40]3[CH:41]=[CH:42][C:37]([NH:36][C:34]([C:27]4[N:28]([CH3:33])[C:29]5[C:25]([CH:26]=4)=[C:24]([O:23][CH3:22])[CH:32]=[CH:31][CH:30]=5)=[O:35])=[C:38]([O:52][CH3:53])[CH:39]=3)[N:12]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 673656514-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-indole-2-carboxamideHCID 178476586HCID 178476586, compound

Product 1

HCID 178487949HCID 178487949, compound

Procedure

Using the procedure described in example 1 step 1f (trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl acetate (0.568 mmol, 200 mg) and 4-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-indole-2-carboxamide (0.568 mmol, 248 mg) gave after purification using column chromatography (silica gel; gradient heptanes/ethyl acetate 1/1 to ethyl acetate) the title compound (245 mg).

Workup

  1. customgave
  2. customafter purification

Sources & evidence

ORD record
ord-98ed52809156492db8a6cfc45585de5f
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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