Carbon tetrabromide → HCID 58528875, compound

HRID 1430989Notes

Reaction equation

HRID 1430989 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:29])[C:11]2[CH:16]=[C:15]([O:17][CH2:18][CH2:19][C:20]3[CH:24]=[CH:23][S:22][CH:21]=3)[CH:14]=[C:13]([O:25][CH:26]([CH3:28])[CH3:27])[CH:12]=2)=[N:7][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:50]>C1COCC1.C(OCC)C>[Br:50][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:29])[C:11]2[CH:16]=[C:15]([O:17][CH2:18][CH2:19][C:20]3[CH:24]=[CH:23][S:22][CH:21]=3)[CH:14]=[C:13]([O:25][CH:26]([CH3:28])[CH3:27])[CH:12]=2)=[N:7][CH:8]=1

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 58528907N-(5-hydroxymethyl-pyridin-2-yl)-3-isopropoxy-5-(2-thiophen-3-yl-ethoxy)-benzamide

Product 1

HCID 58528875HCID 58528875, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(5-Hydroxymethyl-pyridin-2-yl)-3-isopropoxy-5-(2-thiophen-3-yl-ethoxy)-benzamide (0.79 g, 1.92 mmol) in THF (10 mL) was added to a solution of triphenylphosphine (1.03 g, 3.84 mmol) and carbon tetrabromide (1.27 g, 3.84 mmol) in diethyl ether (10 mL). After 16 hours, the reaction mixture was concentrated under reduced pressure and partitioned in EtOAc (30 mL) and water (30 mL). The organic layer was rinsed with water (20 mL), and then a saturated sodium chloride solution (20 mL), dried over sodium sulfate, filtered, and concentrated to yellow oil. After chromatography on silica gel with a gradient from 5-100% ethyl acetate-hexanes, N-(5-bromomethyl-pyridin-2-yl)-3-isopropoxy-5-(2-thiophen-3-yl-ethoxy)-benzamide (0.92 g, 101.3% yield) was obtained, including some impurity, but was used as-is. 1H NMR (300 MHz, DMSO-d6): δ 10.85 (s, 1H), 8.45 (s, 1H), 8.15 (d, J=6.0 Hz, 1H), 7.90 (d, J=6.0 Hz, 1H), 7.45 (d, J=3.0 Hz, 1H), 7.30 (s, 1H), 7.20 (s, 1H), 7.15 (s, 1H), 7.10 (d, J=3.0 Hz, 1H), 6.65 (s, 1H), 4.75 (s, 2H), 4.70 (m, 1H), 4.25 (t, 2H), 3.05 (t, 2H), 1.25 (s, 6H); LCMS (m/z): 477.1 [C22H23BrN2O3S+H]+.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. custompartitioned in EtOAc (30 mL)
  3. washThe organic layer was rinsed with water (20 mL)
  4. dry with materiala saturated sodium chloride solution (20 mL), dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to yellow oil

Sources & evidence

ORD record
ord-69bded544c5a4812bb5a9252401c5094
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

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