Isoquinoline-1-carbaldehyde → HCID 58778962, compound

HRID 1372768Notes

Reaction equation

HRID 1372768 reaction equation
[C:1]1([CH:11]=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[C:16]([F:25])[C:15]=1O.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(O)C>[F:25][C:16]1[C:15]2[O:12][C:11]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][N:2]=3)=[N:13][C:14]=2[CH:19]=[CH:18][C:17]=1[CH2:20][C:21]([O:23][CH3:24])=[O:22]

Participants

5

Reactant 3

HCID 265306Isoquinoline-1-carbaldehydeHCID 12217721Iodo benzene diacetateHCID 17859032Methyl (4-amino-2-fluoro-3-hydroxyphenyl)acetate

Product 1

HCID 58778962HCID 58778962, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (13 ml), isoquinoline-1-carbaldehyde (500 mg, 3.18 mmol) and methyl 4-amino-2-fluoro-3-hydroxyphenylacetate (632 mg, 3.17 mmol) were stirred at room temperature for 2 days. Iodobenzene diacetate (1.23 g, 3.82 mmol) was added, and the reaction mixture was stirred at room temperature for 10 minutes. The reaction mixture was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (3:1, v/v) eluate fractions, methyl (7-fluoro-2-(1-isoquinolinyl)-6-benzoxazolyl)acetate (155 mg, 14%) was obtained as a red brown solid.

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (3:1

Sources & evidence

ORD record
ord-1012462665e0498394f4e929f9f7d78d
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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