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

HRID 505728Notes

Reaction equation

HRID 505728 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]([OH:37])=[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.[C:38](OCC)(=O)C.O1CCCC1.[H][H]>[Pd].CO>[C:15]([C:14]1[CH:13]=[CH:12][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:10][C:9]=1[OH:8])#[N:16]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 667228752-(3-(benzyloxy)-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(3-(benzyloxy)-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid (Example 31; 70 mg, 0.14 mmol), ethyl acetate, tetrahydrofuran, and methanol was treated with 10% palladium on carbon (10 mg) and hydrogenated for four hours at 30 psi hydrogen. The mixture was filtered through Celite, and concentrated to give methyl 2-(4-cyano-3-hydroxyphenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylate (57 mg, 0.14 mmol) as a yellow solid. 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, 8H), 1.61-1.75 (m, 1H), 1.74-1.90 (m, 1H), 2.00-2.12 (m, 1H), 2.16-2.30 (m, 1H), 2.79-2.96 (m, 1H), 3.09 (d, J=16.11 Hz, 1H), 3.57 (ddd, J=13.76, 9.47, 4.70 Hz, 1H), 4.76 (dd, J=9.67, 5.37 Hz, 1H), 6.69 (dd, J=8.86, 1.61 Hz, 1H), 6.82 (s, 1H), 7.36 (d, J=8.59 Hz, 1H), 7.82-7.90 (m, 2H), 8.00 (d, J=8.06 Hz, 1H), 10.70 (s, 1H). ES-MS m/z 402 (M+H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-9b89b75c625b46d0a36ac8449daaf570
Source dataset
uspto-grants-2010_08
Patent number
US07781428B2

Reaction notes

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