Methanamine, hydrochloride (1:1) → 1-[1-[(4-Fluorophenyl)sulfonyl]-5-(4-methoxyphenyl)-1H-pyrrol-3-yl]-N-methylmethanamine

HRID 554395Notes

Reaction equation

HRID 554395 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[CH:14][C:13]([CH:24]=O)=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl-].C[NH3+].[C:29]([BH3-])#[N:30].[Na+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[CH:14][C:13]([CH2:24][NH:30][CH3:29])=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 11637Methanamine, hydrochloride (1:1)HCID 5003444Sodium cyanoborohydrideHCID 866207391-(4-fluorophenylsulfonyl)-5-(4-methoxyphenyl)-1H-pyrrole-3-carbaldehyde

Product 1

HCID 669250331-[1-[(4-Fluorophenyl)sulfonyl]-5-(4-methoxyphenyl)-1H-pyrrol-3-yl]-N-methylmethanamineYield 44.6%

Procedure

Using 1-(4-fluorophenylsulfonyl)-5-(4-methoxyphenyl)-1H-pyrrole-3-carbaldehyde (0.28 g), methylammonium chloride (0.62 g) and sodium cyanoborohydride (0.15 g), a procedure as in Example 6 was performed to give the title compound as a colorless oil (yield 0.13 g, 44%).

Sources & evidence

ORD record
ord-4426c66c964b4cf8ad2a35248b21956f
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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