tert-butyl 3-(1-ethyl-6-fluoro-4-hydroxy-1H-indol-3-yl)piperidine-1-carboxylate → 1-ethyl-6-fluoro-3-(1-methylpiperidin-3-yl)-1H-indol-4-ol

HRID 1404150Notes

Reaction equation

HRID 1404150 reaction equation
C(OC1C(F)=CC=C2C=1C(CCN(C)C)=CN2)C1C=CC=CC=1.[CH2:24]([N:26]1[C:34]2[C:29](=[C:30]([OH:36])[CH:31]=[C:32]([F:35])[CH:33]=2)[C:28]([CH:37]2[CH2:42][CH2:41][CH2:40][N:39]([C:43](OC(C)(C)C)=O)[CH2:38]2)=[CH:27]1)[CH3:25]>>[CH2:24]([N:26]1[C:34]2[CH:33]=[C:32]([F:35])[CH:31]=[C:30]([OH:36])[C:29]=2[C:28]([CH:37]2[CH2:42][CH2:41][CH2:40][N:39]([CH3:43])[CH2:38]2)=[CH:27]1)[CH3:25]

Participants

3

Reactant 2

HCID 58303841tert-butyl 3-(1-ethyl-6-fluoro-4-hydroxy-1H-indol-3-yl)piperidine-1-carboxylateHCID 669270882-(4-Benzyloxy-5-fluoro-1H-indol-3-yl)-N,N-dimethylethanamine

Product 1

HCID 509963471-ethyl-6-fluoro-3-(1-methylpiperidin-3-yl)-1H-indol-4-olYield 22%

Procedure

Following the procedure (step 6, scheme 1) used to prepare compound 1-7a, compound 38-5 gave compound 38-6 (20 mg, 22%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ (ppm) 9.91 (s, 1H), 6.92 (s, 1H), 6.63 (dd, J=10.2, 2.1 Hz, 1H), 6.14 (dd, J=11.5, 2.1 Hz, 1H), 3.98 (q, J=7.1 Hz, 2H), 3.31 (m, 1H), 3.02 (d, J=10.1 Hz, 1H), 2.71 (s, 1H), 2.14 (s, 3H), 2.01-1.42 (m, 5H), 1.25 (m, J=7.2 Hz, 4H). LCMS: calc 276.2 and found: 277.1 [MH]+.

Sources & evidence

ORD record
ord-09528da2dc4d4af2add42c2e10700a29
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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