Triethylamine → HCID 86668000, compound

HRID 2179381Notes

Reaction equation

HRID 2179381 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:22][OH:23])[C:5]2[O:14][C:13]3[CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][C:8]=3[C:6]=2[CH:7]=1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33].C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:22][O:23][S:32]([CH3:31])(=[O:34])=[O:33])[C:5]2[O:14][C:13]3[CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:9][C:8]=3[C:6]=2[CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 68109355HCID 68109355, compound

Product 1

HCID 86668000HCID 86668000, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of the product of Example 74, step E (300 mg, 0.78 mmol) in dichloromethane (4 mL) at 0° C. was added triethylamine (93 mg, 0.92 mmol) followed by methanesulfonyl chloride (100 mg, 0.88 mmol). The reaction mixture was allowed to warm to ambient temperature over 2 h, then treated with saturated sodium bicarbonate solution and extracted with dichloromethane. The organic extracts were dried over sodium sulphate, filtered, and concentrated in vacuo. Purification by flash chromatography (SiO2, 95:5 hexanes/ethyl acetate) provided tert-butyl 8-bromo-6-((methylsulfonyloxy)methyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (340 mg, 94%) as a yellow solid: 1H NMR (CDCl3, 300 MHz) δ 7.59 (s, 1H), 7.44 (s, 1H), 5.47 (s, 2H), 4.52 (s, 2H), 3.83 (t, J=5.1 Hz, 2H), 3.02 (s, 3H), 2.88 (s, 2H), 1.51 (s, 9H).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic extracts were dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (SiO2, 95:5 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-d995906d864940fa80d44f031dae2f33
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

Loading…