4-(tert-Butoxycarbonylaminomethyl)phenylboronic acid → HCID 57900451, compound

HRID 1949889Notes

Reaction equation

HRID 1949889 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:6][CH2:7][CH2:8][C:9]3[CH:15]=[CH:14][S:13][C:10]=3[C:11]=2[N:12]=1.[C:16]([NH:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>>[N:12]1[C:11]2[C:10]3[S:13][C:14]([C:28]4[CH:29]=[CH:30][C:25]([CH2:24][NH:23][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[CH:26][CH:27]=4)=[CH:15][C:9]=3[CH2:8][CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 38631634-(tert-Butoxycarbonylaminomethyl)phenylboronic acidHCID 86634850HCID 86634850, compound

Product 1

HCID 57900451HCID 57900451, compound

Procedure

Following Scheme 5, 2-bromo-6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepine and 4-(N-Boc-aminomethyl)-phenylboronic acid were reacted to give tert-butyl 4-(6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)benzylcarbamate. MS: (ESI+)=409.1. Hydrogen chloride in dioxane (4 ml, 4 N) was added to a solution of 67 mg (0.16 mmol) of tert-butyl 4-(6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)benzylcarbamate in 6 ml of methylene chloride and the mixture was stirred for 2 hours. The precipitate was collected, washed with methylene chloride and ethyl ether and dried in vacuum to give 335 (34 mg, 55%). MS: (ESI+) 309.1.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-2efd842fdb624e8cb79b4b84ba980cc4
Source dataset
uspto-grants-2013_03
Patent number
US08399690B2

Reaction notes

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