4-Fluoro-1-naphthaleneboronic Acid (contains varying amounts of Anhydride) → 5-(4-Fluoronaphth-1-yl)-3-(1-Methylpiperidin-4-yl)-4-Aza-1H-Indole

HRID 278006Notes

Reaction equation

HRID 278006 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.[F:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29](B(O)O)=[CH:28][CH:27]=1>>[F:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([C:7]2[N:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][CH:11]=[C:10]3[CH:16]2[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]2)=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 27826754-Fluoro-1-naphthaleneboronic Acid (contains varying amounts of Anhydride)HCID 120418125-Trifluoromethanesulfonyloxy-3-(1-methylpiperidin-4-yl)pyrrolo[3,2-b]pyridine

Product 1

HCID 99068535-(4-Fluoronaphth-1-yl)-3-(1-Methylpiperidin-4-yl)-4-Aza-1H-IndoleYield 84.5%

Procedure

O-Trifluoromethanesulfonyl-3-(1-methylpiperidin-4-yl)-5-hydroxy-4-aza-1H-indole (160 mg, 0.441 mmol) and 4-fluoronaphth-1-ylboronic acid (134 mg, 0.71 mmol) were converted to 134 mg of the title compound by the procedure of Example 3. (85%). MS(FD) m/e 359.8 (M+). EA calculated for C23H22FN3: C, 76.88; H, 6.13; N, 11.70. Found: C, 77.15; H, 6.21; N, 11.62.

Sources & evidence

ORD record
ord-6f18ed2c042c401e8a117d162e56db05
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

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