HCID 178420405, compound → HCID 178517572, compound

HRID 1681277Notes

Reaction equation

HRID 1681277 reaction equation
C([O:8][C:9]1[C:17]2[C:12]([NH:13][CH:14]=[CH:15][CH:16]=2)=[CH:11][N:10]=1)C1C=CC=CC=1>[Pd].C(O)C>[OH:8][C:9]1[C:17]2[C:12]([NH:13][CH:14]=[CH:15][CH:16]=2)=[CH:11][N:10]=1

Participants

4

Reactant 1

HCID 178420405HCID 178420405, compound2×

Product 1

HCID 178517572HCID 178517572, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-benzyloxypyrrolo[3,4-b]pyridine (Compound 7f, 1.38 g, 6.15 mmol), 5% Pd/C (0.30 g), and absolute ethanol (25 mL) was shaken under a hydrogen atmosphere (3 atm) for 30 minutes. The resulting mixture was filtered through diatomaceous earth (Celite (trademark)), and the filtrate was evaporated under reduced pressure. The residual solid was triturated in ethyl ether to yield Compound 7i (0.80 g, 5.96 mmol, 97%) as an off-white crystalline solid: mp, 280.0°-282.0° C.: IR (KBr) 1,640, 1,615, 1,605, 1,455, 1,430, 1,400, 1,380, 1,365 cm-1 ; 1H NMR (DMSO-d6) δ 11.4 (br m, 2H), 7.56 (d, J=9.7 Hz, 1H), 7.16 (d, J=3.1 Hz, 1H), 6.01-5.93 (m, 2H); 13C NMR (DMSO-d6) 162.0, 131.9, 127.9, 125.0, 118.2, 112.2, 94.5; LRMS (m/z, relative intensity) 135 (41), 134 (M+, 100), 106 (66), 105 (42), 79 (59), 53 (31), 52 (52). Anal. calcd. for C7H6N2O: C, 62.68; H, 4.51; N, 20.88; found: C, 62.40; H, 4.40; N, 20.76.

Workup

  1. filtrationThe resulting mixture was filtered through diatomaceous earth (Celite (trademark))
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residual solid was triturated in ethyl ether

Sources & evidence

ORD record
ord-5b75e81d8736400ab1d65fb0aeef24f8
Source dataset
uspto-grants-1992_12
Patent number
US05169947

Reaction notes

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