methyl 2-(3-(benzyloxy)-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylate → methyl 2-(4-cyano-3-hydroxyphenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylate

HRID 505727Notes

Reaction equation

HRID 505727 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([N:17]2[CH:25]([CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[CH:24]3[C:19]([C:20]4[CH:34]=[CH:33][C:32]([C:35]([O:37][CH3:38])=[O:36])=[CH:31][C:21]=4[CH2:22][CH2:23]3)=[N:18]2)[CH:12]=[CH:13][C:14]=1[C:15]#[N:16])C1C=CC=CC=1.[H][H]>[Pd].C(OCC)(=O)C>[C:15]([C:14]1[CH:13]=[CH:12][C:11]([N:17]2[CH:25]([CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[CH:24]3[C:19]([C:20]4[CH:34]=[CH:33][C:32]([C:35]([O:37][CH3:38])=[O:36])=[CH:31][C:21]=4[CH2:22][CH2:23]3)=[N:18]2)=[CH:10][C:9]=1[OH:8])#[N:16]

Participants

5

Reactant 2

HCID 66722631methyl 2-(3-(benzyloxy)-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 66722719methyl 2-(4-cyano-3-hydroxyphenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylateYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 2-(3-(benzyloxy)-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylate, Example 30, (345 mg, 0.68 mmol), catalytic 10% palladium on carbon, and ethyl acetate was hydrogenated at 30 psi hydrogen for three hours. The mixture was filtered through Celite and concentrated. The solid was suspended in diethyl ether/hexanes, a small amount of methanol and filtered to give methyl 2-(4-cyano-3-hydroxyphenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylate (150 mg, 0.36 mmol, 53% yield). The title compound was largely present as (±)-(3RS,3aSR)-methyl 2-(4-cyano-3-hydroxyphenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylate. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.10-1.58 (m, 7H), 1.60-1.90 (m, 2H), 2.06 (s, 1H), 2.16-2.30 (m, 1H), 2.79-2.95 (m, 1H), 3.05-3.15 (m, 1H), 3.58 (ddd, J=13.76, 9.47, 4.70 Hz, 1H), 3.86 (s, 3H), 4.77 (dd, J=9.67, 5.37 Hz, 1H), 6.70 (d, J=8.59 Hz, 1H), 6.82 (s, 1H), 7.36 (d, J=8.86 Hz, 1H), 7.82-7.93 (m, 2H), 8.02 (d, J=8.06 Hz, 1H), 10.70 (s, 1H). ES-MS m/z 416 (M+H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated
  3. filtrationa small amount of methanol and filtered

Sources & evidence

ORD record
ord-0feaf4da71fb4b359bec13d81b3626d7
Source dataset
uspto-grants-2010_08
Patent number
US07781428B2

Reaction notes

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