2-Thiopheneboronic acid → 5-(Thien-2-yl)-3-(1-Methylpiperidin-4-yl)-4-Aza-1H-Indole

HRID 278004Notes

Reaction equation

HRID 278004 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.[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1B(O)O>>[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]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[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]1

Participants

3

Reactant 2

HCID 27339602-Thiopheneboronic acidHCID 120418125-Trifluoromethanesulfonyloxy-3-(1-methylpiperidin-4-yl)pyrrolo[3,2-b]pyridine

Product 1

HCID 98610255-(Thien-2-yl)-3-(1-Methylpiperidin-4-yl)-4-Aza-1H-IndoleYield 66.5%

Procedure

O-Trifluoromethanesulfonyl-3-(1-methylpiperidin-4-yl)-5-hydroxy-4-aza-1H-indole (158 mg, 0.435 mmol) and 2-thiopheneboronic acid (83 mg, 0.653 mmol) were converted to 86 mg of the title compound by the procedure of Example 1 except that a wash with 3:1 chloroform:isopropanol was performed between the base and brine and the solvent system for chromatography was 0-5% methanol/dichloromethane. (67%). MS(FD) m/e 297.2 (M+). EA calculated for C17H19SN3: C, 68.69; H, 6.40; N, 14.14. Found: C, 69.02; H, 6.49; N, 14.23.

Sources & evidence

ORD record
ord-56b827e9addf42b08707cdda5657a57c
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

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