4-Methoxy-2,3-dihydrobenzofuran-3-amine → HCID 178488327, compound

HRID 1695620Notes

Reaction equation

HRID 1695620 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:17]=[C:18]=S)=[C:6]([CH:16]=1)[CH2:7][O:8][Si](C(C)(C)C)(C)C.[CH3:20][O:21][C:22]1[C:27]2[CH:28]([NH2:31])[CH2:29][O:30][C:26]=2[CH:25]=[CH:24][CH:23]=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:17]=[C:18]([NH:31][CH:28]3[C:27]4[C:22]([O:21][CH3:20])=[CH:23][CH:24]=[CH:25][C:26]=4[O:30][CH2:29]3)[O:8][CH2:7][C:6]=2[CH:16]=1

Participants

3

Reactant 2

HCID 672125224-Methoxy-2,3-dihydrobenzofuran-3-amineHCID 87311762(5-Bromo-2-isothiocyanato-benzyloxy)-tert-butyl-dimethyl-silane

Product 1

HCID 178488327HCID 178488327, compoundYield 50%

Procedure

Prepared from (5-bromo-2-isothiocyanato-benzyloxy)-tert-butyl-dimethyl-silane (Example 32, step B) (4.0 g, 11.2 mmol) and rac-4-methoxy-2,3-dihydro-benzofuran-3-ylamine (Example 5, step B) (1.84 g, 11.2 mmol) according to the procedure described for Example 1. Obtained the title compound as a white solid (2.09 g, 50%), m.p. 132.5° C.; MS (ISP) m/e=375.1 [(M+H)+].

Sources & evidence

ORD record
ord-551518b1aedd4dd9ad48d47d0ee41f83
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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