Borane → HCID 45137884, compound

HRID 221384Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=2)[C:22]([N:24]([CH3:26])[CH3:25])=O)(=[O:17])=[O:16])=[CH:11][CH:10]=1.B.[Cl-].[NH4+]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:29]=[CH:28][CH:27]=[C:21]([CH2:22][N:24]([CH3:26])[CH3:25])[CH:20]=2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 3-(2′,4′-dichlorobiphenyl-4-ylsulfonamido)-N,N-dimethylbenzamide (130 mg, 0.29 mmol) in THF (5 mL) was stirred at room temperature and 1 M borane in THF (1.45 mL, 1.45 mmol) was added. The solution was heated at 50° C. for 45 minutes. The mixture was then cooled and saturated ammonium chloride (5 mL) was added. The mixture was further diluted with water (10 mL) and extracted with EtOAc (3×15 mL). The combined organic layers were dried over MgSO4, filtered and evaporated. The residue was purified by column chromatography (SiO2, 20% acetone/hexane) and the title compound obtained as a light yellow glass (73 mg). 1H NMR (300 MHz, CDCl3): δ 2.49 (6H, s), 3.87 (2H, s), 6.69 (1H, br s), 7.05-7.35 (6H, m), 7.49-7.50 (3H, m) and 7.81 (2H, d, J=9 Hz). MS, m/z: Calcd, 434.062. Found, 434.17 (M).

Workup

temperatureThe mixture was then cooled
extractionextracted with EtOAc (3×15 mL)
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
customevaporated
customThe residue was purified by column chromatography (SiO2, 20% acetone/hexane)

Sources & evidence

ORD record: ord-e834c5ff1ca549bc9a5926e75d0a553f
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207167B2

Reaction notes

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