3-Ethynyloxolan-3-ol → (+/-)-9-Fluoro-10-((3-hydroxytetrahydrofuran-3-yl)ethynyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575210Notes

Reaction equation

HRID 575210 reaction equation
Br[C:2]1[C:3]([F:19])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[CH:12]=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:18]=1.[C:20]([C:22]1([OH:27])[CH2:26][CH2:25][O:24][CH2:23]1)#[CH:21]>>[F:19][C:3]1[C:2]([C:21]#[C:20][C:22]2([OH:27])[CH2:26][CH2:25][O:24][CH2:23]2)=[CH:18][C:6]2[C:7]3[N:8]([CH:12]=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=3)[CH2:9][CH2:10][O:11][C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 156999173-Ethynyloxolan-3-olHCID 8669305110-Bromo-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 86693216(+/-)-9-Fluoro-10-((3-hydroxytetrahydrofuran-3-yl)ethynyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 19%

Procedure

Similar to as described in General Procedure G, 10-bromo-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide was reacted with 3-ethynyloxolan-3-ol (US2010/144757 A1, 2010) to give the titled compound as a light brown solid (41 mg, 19%).

Sources & evidence

ORD record
ord-2b7a02a7a3d847ee84a2f221e062dc90
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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