(Naphthalen-2-yl)boronic acid → 5-(Naphth-2-yl)-3-(1-Methylpiperidin-4-yl)-4-Aza-1H-Indole

HRID 278005Notes

Reaction equation

HRID 278005 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.[CH:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1B(O)O>>[CH:33]1[C:34]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:30]=[CH:31][C:32]=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 2734375(Naphthalen-2-yl)boronic acidHCID 120418125-Trifluoromethanesulfonyloxy-3-(1-methylpiperidin-4-yl)pyrrolo[3,2-b]pyridine

Product 1

HCID 99279655-(Naphth-2-yl)-3-(1-Methylpiperidin-4-yl)-4-Aza-1H-IndoleYield 91.8%

Procedure

O-Trifluoromethanesulfonyl-3-(1-methylpiperidin-4-yl)-5-hydroxy-4-aza-1H-indole (164 mg, 0.450 mmol) and 2-naphthylboronic acid (124 mg, 0.720 mmol) were converted to 141 mg of the title compound by the procedure of Example 3. (91%). MS(FD) m/e 341.8 (M+). EA calculated for C23H23N3: C, 80.94; H, 6.74; N, 12.32. Found: C, 88.11; H, 6.87; N, 12.27.

Sources & evidence

ORD record
ord-9ac361d242d04deba14e57bacb2f6bbb
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

Loading…