1-Methyl-4-(prop-2-yn-1-yl)benzene → (R)-5,5-Difluoro-4-[5-fluoro-2-(4-methyl-benzyl)-3H-indol-6-yl]-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine

HRID 1626142Notes

Reaction equation

HRID 1626142 reaction equation
[NH2:1][C:2]1[C:3](I)=[CH:4][C:5]([F:18])=[C:6]([C@:8]2([CH3:17])[C:13]([F:15])([F:14])[CH2:12][O:11][C:10]([NH2:16])=[N:9]2)[CH:7]=1.[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]#[CH:29])=[CH:23][CH:22]=1>>[F:14][C:13]1([F:15])[CH2:12][O:11][C:10]([NH2:16])=[N:9][C@@:8]1([C:6]1[CH:7]=[C:2]2[C:3]([CH2:29][C:28]([CH2:27][C:24]3[CH:25]=[CH:26][C:21]([CH3:20])=[CH:22][CH:23]=3)=[N:1]2)=[CH:4][C:5]=1[F:18])[CH3:17]

Participants

3

Reactant 2

HCID 193712311-Methyl-4-(prop-2-yn-1-yl)benzeneHCID 58304250(R)-4-(5-amino-2-fluoro-4-iodo-phenyl)-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine

Product 1

HCID 71009188(R)-5,5-Difluoro-4-[5-fluoro-2-(4-methyl-benzyl)-3H-indol-6-yl]-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamineYield 73%

Procedure

In a manner analogous to that described in Example 39, the coupling and cyclisation reaction of (R)-4-(5-amino-2-fluoro-4-iodo-phenyl)-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine (intermediate B6.1) with 1-methyl-4-prop-2-ynyl-benzene yielded the title compound (73% yield) as a light green foam. MS (ISP): m/z=388.3 [M+H]+.

Sources & evidence

ORD record
ord-f74d1fab8d35433fbe5a486e2ba82a2d
Source dataset
uspto-grants-2014_07
Patent number
US08785436B2

Reaction notes

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