HCID 178420405, compound → HCID 178517572, compound

HRID 728766Notes

Reaction equation

HRID 728766 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 filtratewas evaporated under reduced pressure. The residual solid was triturated inethyl 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) 1640, 1615, 1605, 1455, 1430, 1400, 1380, 1365 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 filtratewas evaporated under reduced pressure
  3. customThe residual solid was triturated inethyl ether

Sources & evidence

ORD record
ord-cc63cc007b4a49228eeb4d24a54708a7
Source dataset
uspto-grants-1991_09
Patent number
US05051412

Reaction notes

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