5-Trifluoromethanesulfonyloxy-3-(1-methylpiperidin-4-yl)pyrrolo[3,2-b]pyridine → 5-(Benzimidazol-2-yl)-3-(1-Methylpiperidin-4-yl)-4-Aza-1H-Indole

HRID 278009Notes

Reaction equation

HRID 278009 reaction equation
FC(F)(F)S(O[C:7]1[N:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1)(=O)=O.C(OC([N:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[C:33]1Cl)=O)(C)(C)C>>[N:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[NH:34][C:33]=1[C:7]1[N:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 120418125-Trifluoromethanesulfonyloxy-3-(1-methylpiperidin-4-yl)pyrrolo[3,2-b]pyridineHCID 23441223tert-Butyl 2-chloro-1H-benzo[d]imidazole-1-carboxylate

Product 1

HCID 99275485-(Benzimidazol-2-yl)-3-(1-Methylpiperidin-4-yl)-4-Aza-1H-Indole

Procedure

O-Trifluoromethanesulfonyl-3-(1-methylpiperidin-4-yl)-5-hydroxy-4-aza-1H-indole (150 mg, 0.413 mmol) and 1-t-butyloxycarbonyl-2-chlorobenzimidazole (104 mg, 0.413 mmol) were converted to the title compound by the procedure of Example 7 except that after chromatography there was a mixture of protected and de-protected products. Therefore, 80 mg of the mixture was dissolved in 20 mL of dichloromethane and 1 mL of trifluoroacetic acid was added. The mixture was stirred for 2 hours and then taken up in water. The reaction was partitioned between 3 mL of 1N aqueous sodium hydroxide and 3 mL of 3:1 chloroform:isopropanol to give 51.2 mg. (37%). MS(FD) m/e 331.8 (M+).

Sources & evidence

ORD record
ord-7ca7e6174b9d48e9861f4047a04ecccc
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

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