Ammonium Hydroxide → HCID 67980295, compound

HRID 1260158Notes

Reaction equation

HRID 1260158 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14](CC(O)=O)[NH:15]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([C:29]1[NH:30]C=CN=1)(C1NC=CN=1)=O.[OH-:34].[NH4+]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH2:22][C:29]([NH2:30])=[O:34])=[CH:14][NH:15]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 67980091HCID 67980091, compound

Product 1

HCID 67980295HCID 67980295, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-benzyloxyindole-acetic acid (4.72 g, 16.7 mmol) in tetrahydrofuran (100 mL), was added carbonyl diimidazole (2.85 g, 17.6 mmol). The resulting solution was stirred at room temperature for 1.5 hr. Ammonium hydroxide (14 mL) was added and the reaction was allowed to stir at room temperature for 18 h. The mixture was concentrated to ½ volume and the resulting solid filtered and washed with cold methanol to give 2-[6-(benzyloxy)-1H-indol-3-yl]acetamide (4.7 g, quantitative) as a off-white solid. Mp: 189-192° C.; 1H NMR (DMSO-d6) 400 MHz δ: 10.65 (brs, 1H), 7.46 (d, J=7.4 Hz, 2H), 7.37-7.35 (m, 2H), 7.31 (m, 1H), 7.26 (brs, 1H), 7.14 (d, J=2.3 Hz, 1H), 7.12 (d, J=2.3 Hz, 1H), 6.79 (m, 2H), 5.04 (s, 2H), 3.39 (s, 2H); LCMS [M+H]: 281.

Workup

  1. stirringto stir at room temperature for 18 h
  2. concentrationThe mixture was concentrated
  3. filtrationthe resulting solid filtered
  4. washwashed with cold methanol

Sources & evidence

ORD record
ord-acce3c2436764c19847ddacda59ff964
Source dataset
uspto-grants-2013_06
Patent number
US08470786B2

Reaction notes

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