(Dimethyl sulfide)trihydroboron → HCID 9913858, compound

HRID 1757242Notes

Reaction equation

HRID 1757242 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][C@@H:15]2[CH2:20][CH2:19][CH2:18][N:17]([C:21]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=O)[C@@H:16]2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CSC.B>>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([CH2:13][O:14][C@@H:15]2[CH2:20][CH2:19][CH2:18][N:17]([CH2:21][C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)[C@@H:16]2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:4]=[C:3]([C:2]([F:35])([F:34])[F:1])[CH:8]=1

Participants

3

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 53774065HCID 53774065, compound

Product 1

HCID 9913858HCID 9913858, compound

Procedure

The compound of Example 13 was reacted with borane dimethylsulfide as described in Example 10. The free base was recrystallised from ether and hexane to give the product as a white crystalline solid. 1H NMR (250 MHz, CDCl3) d 1.44-1.64 (2H, m, CH2), 1.9-2.2 (2H, m, CH2), 2.24 (1H, d, J=7 Hz, CHN), 3.14 (1H, d, J=7 Hz, CHN), 3.4 (1H, s, CHO), 3.56 (1H, s, NCHPh), 3.6 (1H, s, CH-thiophene), 4.88 (1H, d, J=10 Hz, CH-thiophene), 4.0 (1H, d, J=10 Hz, CHAr), 4.24 (1H, d, J=10 Hz, CHAr), 6.7 (1H, d, J=1 Hz, thiophene-H), 6.9 (H, dd, J=2 Hz, 3 Hz, thiophene-H), 7.2 (1H, d, J=3 Hz, thiophene-H), 7.28 (4H, m, Ar--H), 7.5 (3 H, m, Ar--H), 7.68 (1H, s, Ar--H). MS m/z 500 (M+, 100%).

Workup

  1. customThe free base was recrystallised from ether and hexane

Sources & evidence

ORD record
ord-cffc0979adae4087ac2b6145f4539fbd
Source dataset
uspto-grants-1995_08
Patent number
US05444074

Reaction notes

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