Dimethylformamide → HCID 59023748, compound

HRID 1678262Notes

Reaction equation

HRID 1678262 reaction equation
[S:1]1[C:5]([C:6]2[CH:7]=[C:8](Br)[CH:9]=[C:10]3[C:14]=2[NH:13][N:12]=[CH:11]3)=[CH:4][C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]1=2.C([Sn](CCCC)(CCCC)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)CCC.C(N(CC)CC)C.CN(C)[CH:48]=[O:49]>>[S:1]1[C:5]([C:6]2[CH:7]=[C:8]([C:48]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:49])[CH:9]=[C:10]3[C:14]=2[NH:13][N:12]=[CH:11]3)=[CH:4][C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]1=2

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 607632TributylphenyltinHCID 59024282HCID 59024282, compound

Product 1

HCID 59023748HCID 59023748, compoundYield 8.5%

Conditions

Temperature
90 °C

Procedure

A mixture of 7-benzo[b]thiophen-2-yl-5-bromo-1H-indazole (Preparation #26, 0.25 g, 0.76 mol), tributylphenyltin (0.56 g, 1.52 mmol), triethylamine (0.23 g, 2.28 mmol) and trans-dichloro[bis(triphenylphosphine)]palladium (II) (0.08 g, 0.114 mmol) in N,N-dimethylformamide (4 mL) was purged with carbon monoxide then stirred under an atmosphere of carbon monoxide at about 90° C. in an oil bath for about 2 hours. The solvent was removed in vacuo and the residue was applied to a silica gel column then eluted with dichloromethane/methanol (95:5). The fractions that contained product were combined and triturated with heptane then the solids were collected by filtration and purified by preparative reverse phase HPLC to give (7-Benzo[b]thiophen-2-yl-1H-indazol-5-yl)-phenyl-methanone(23 mg, 8.5%); (DMSO-d6, 400 MHz) δ 13.85 (bs, 1H), 8.49 (bs, 1H), 8.27 (s, 1H), 8.18 (bs, 1H), 8.06 (m, 2H), 7.93 (m, 1H), 7.81 (m, 2H), 7.71 (m, 1H), 7.61 (m, 2H), 7.45 (m, 2H); RP-HPLC (Table 1, Method e) Rt 2.50 min; m/z: (M+H)+ 353.0.

Workup

  1. customwas purged with carbon monoxide
  2. customThe solvent was removed in vacuo
  3. washthen eluted with dichloromethane/methanol (95:5)
  4. customtriturated with heptane
  5. filtrationthe solids were collected by filtration
  6. custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-6e61c38d56094061904d9ebb37b3c25a
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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