Sodium borohydride → HCID 66924921, compound

HRID 554351Notes

Reaction equation

CO.[CH3:3][NH2:4].[BH4-].[Na+].[Br:7][C:8]1[N:12]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:11]=[C:10]([CH:22]=O)[C:9]=1[CH:24]([CH3:26])[CH3:25]>>[Br:7][C:8]1[N:12]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:11]=[C:10]([CH2:22][NH:4][CH3:3])[C:9]=1[CH:24]([CH3:26])[CH3:25]

Participants

Reactant 3

HCID 4311764Sodium borohydride

HCID 57454252Monomethylamine methanol

HCID 86620770HCID 86620770, compound

Product 1

HCID 66924921HCID 66924921, compoundYield 12.6%

Procedure

Using methyl 5-bromo-4-isopropyl-1-(phenylsulfonyl)-1H-pyrrole-3-carboxylate (4.8 g), and a 1.5 mol/L solution (50 mL) of diisobutylaluminum hydride in toluene, tetra-n-propylammonium perruthenate (218 mg), N-methylmorpholine N-oxide (1.6 g) and molecular sieves 4A powder (2.5 g), a procedure as in Reference Example 6 was performed to give crude 5-bromo-4-isopropyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde (3.83 g) as an oil. Furthermore, using 40% methylamine methanol solution (877 mg), sodium borohydride (474 mg) and crude 5-bromo-4-isopropyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde (3.83 g), a procedure as in Reference Example 66 was performed to give the title compound as a colorless oil (yield 502 mg, 11%).

Sources & evidence

ORD record: ord-bc21b5d3365a498aa5b1f4cefd00dbc2
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048909B2

Reaction notes

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