Dimethylamine → HCID 67286596, compound

HRID 529258Notes

Reaction equation

HRID 529258 reaction equation
Br[CH2:2][C:3]1[O:7][C:6]2[C:8]([O:14]C(=O)C)=[C:9]([O:12][CH3:13])[CH:10]=[CH:11][C:5]=2[C:4]=1[C:18](=[O:31])[C:19]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=1.[CH3:32][NH:33][CH3:34]>C1COCC1>[CH3:32][N:33]([CH:2]=[C:3]1[O:7][C:6]2[C:8]([OH:14])=[C:9]([O:12][CH3:13])[CH:10]=[CH:11][C:5]=2[CH:4]1[C:18](=[O:31])[C:19]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=1)[CH3:34]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 59138491HCID 59138491, compound

Product 1

HCID 67286596HCID 67286596, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-bromomethyl-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-7-acetoxy-benzo[b]furan (Example 33) (25 mg, 0.051 mmol) in dry THF (0.5 mL) was added solution of dimethylamine (0.5 mL, excess, 2M solution in THF) and the mixture was stirred for 6 hours at room temperature (tlc). The solvent was distilled and the crude was purified over silica gel to afford the title compound as a light yellow solid (15 mg, 71%). 1H NMR (300 MHz, CDCl3) δ−7.14 (s, 2H, benzoyl Hs), 6.85 (s, 2H, Ar—Hs), 3.93 (s, 3H, OMe), 3.92 (s, 3H, OMe), 3.81 (s, 6H, 2×OMe), 3.75 (s, 2H), 2.31 (s, 6H).

Workup

  1. distillationThe solvent was distilled
  2. customthe crude was purified over silica gel

Sources & evidence

ORD record
ord-7f219afc40b64e18a88a4c0385a884f5
Source dataset
uspto-grants-2016_05
Patent number
US09346842B2

Reaction notes

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