Lithium Hydroxide → HCID 58215646, compound

HRID 1661560Notes

Reaction equation

HRID 1661560 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]#[N:21])=[CH:17][CH:18]=3)[C:13]([CH3:22])=[C:12]2[C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[CH:6][CH:5]=1.[OH-].[Li+]>CO.C1COCC1>[C:20]([C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][CH:17]=1)[N:11]([CH2:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:29])=[O:2])=[CH:9][CH:8]=1)[C:12]([C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)=[C:13]2[CH3:22])#[N:21]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67093316HCID 67093316, compound

Product 1

HCID 58215646HCID 58215646, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Cyano-3-methyl-2-pyridin-3-yl-indole (Example 6) is processed according to the method described in Example 11 to give 4-(5-cyano-3-methyl-2-pyridin-3-yl-indol-1-ylmethyl)-benzoic acid methyl ester. To a solution of 4-(5-cyano-3-methyl-2-pyridin-3-yl-indol-1-ylmethyl)-benzoic acid methyl ester (80 mg, 0.21 mmol) in methanol (5 mL) and THF (5 mL) is added 1M aqueous lithium hydroxide (2.5 mL, 2.5 mmol) and the mixture is stirred overnight at ambient temperature. The volatiles are removed in vacuo and the residue is redissolved in DMF and purified by Xbridge RP18 with a gradient of 0.1% aqueous ammonium hydroxide in acetonitrile to give 4-(5-cyano-3-methyl-2-pyridin-3-yl-indol-1-ylmethyl)-benzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.25 (s, 3H), 5.40 (s, 2H), 6.71 (d, J=8.1 Hz, 2H), 7.47-7.55 (m, 2H), 7.66 (t, J=8.6 Hz, 3H), 7.79-7.83 (m, 1H), 8.20 (d, J=1.3 Hz, 1H), 8.58 (d, J=1.5 Hz, 1H), 8.64 (dd, J=4.8, 1.5 Hz, 1H). HRMS (ESI) m/z 368.1396 [(M+H)+ Calcd for C23H18N3O2: 368.1399].

Workup

  1. customThe volatiles are removed in vacuo
  2. dissolutionthe residue is redissolved in DMF
  3. custompurified by Xbridge RP18 with a gradient of 0.1% aqueous ammonium hydroxide in acetonitrile

Sources & evidence

ORD record
ord-9da159370d8f4104ae328e638ad7881d
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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