Methanesulfonyl chloride → Methyl 10-bromo-9-fluoro-3-((1-methyl-1H-pyrazol-5-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylate

HRID 575409Notes

Reaction equation

HRID 575409 reaction equation
BrC1C(F)=CC2C3CC(C3)N3C(CC4N(C)N=CC=4)=C(C(OC)=O)N=C3C=2C=1.[Br:29][C:30]1[C:31]([F:56])=[CH:32][C:33]2[O:39][CH2:38][CH2:37][N:36]3[C:40]([CH:47](O)[C:48]4[N:52]([CH3:53])[N:51]=[CH:50][CH:49]=4)=[C:41]([C:43]([O:45][CH3:46])=[O:44])[N:42]=[C:35]3[C:34]=2[CH:55]=1.CS(Cl)(=O)=O.[H][H]>[Pd]>[Br:29][C:30]1[C:31]([F:56])=[CH:32][C:33]2[O:39][CH2:38][CH2:37][N:36]3[C:40]([CH2:47][C:48]4[N:52]([CH3:53])[N:51]=[CH:50][CH:49]=4)=[C:41]([C:43]([O:45][CH3:46])=[O:44])[N:42]=[C:35]3[C:34]=2[CH:55]=1

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 86693425Methyl 10-bromo-9-fluoro-3-[hydroxy-(2-methylpyrazol-3-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benz oxazepine-2-carboxylateHCID 86693454Methyl 10-bromo-9-fluoro-3((1-methyl-1H-pyrazol-5-yl)methyl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86693460Methyl 10-bromo-9-fluoro-3-((1-methyl-1H-pyrazol-5-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Methyl 10-bromo-9-fluoro-3-((1-methyl-1H-pyrazol-5-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylate was prepared similarly to methyl 10-bromo-9-fluoro-3-((1-methyl-1H-pyrazol-5-yl)methyl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate. Methyl 10-bromo-9-fluoro-3-(hydroxy(1-methyl-1H-pyrazol-5-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylate was reacted with methanesulfonyl chloride followed by palladium on carbon and hydrogen to afford 105 mg (85% crude yield) of the titled crude product which was carried forward without further purification.

Sources & evidence

ORD record
ord-47efdaba59a74e459795f06b6f04b3bd
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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