Carbon tetrabromide → HCID 57546057, compound

HRID 913862Notes

Reaction equation

HRID 913862 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([CH:12](O)[CH3:13])[C:9]2[C:5](=[CH:6][N:7]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:8]=2)[CH:4]=1.C(Br)(Br)(Br)[Br:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.CCCCC>[Br:24][CH:12]([C:10]1[C:9]2[C:5](=[CH:6][N:7]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:8]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=1)[CH3:13]

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 57546015HCID 57546015, compound

Product 1

HCID 57546057HCID 57546057, compound

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (±)-1-(5-methoxy-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)ethanol (712 mg, 2.21 mmol) and carbon tetrabromide (1.10 g, 3.31 mmol) in tetrahydrofuran (10 mL) at 0° C. was added triphenylphosphine (869 mg, 3.31 mmol). The resulting solution was stirred at room temperature for 30 min. The reaction was diluted with several volumes of pentane and filtered to remove undissolved solids. The organics were concentrated and purified by column chromatography (5% 30% EtOAc/Hex) to give 240 mg (28.2%) as colorless oil. 1H-NMR (CDCl3, 300 MHz) δ 7.95 (s, 1H), 7.15 (s, 1H), 6.82 (s, 1H), 5.84 (q, J=6.0 Hz, 1H), 5.67 (s, 2H), 3.8 (s, 3H), 3.62 (m, 2H), 2.94(d, J=6.0 Hz, 2H), 0.9 (m, 2H), −0.06 (s, 9H).

Workup

  1. filtrationfiltered
  2. customto remove undissolved solids
  3. concentrationThe organics were concentrated
  4. custompurified by column chromatography (5% 30% EtOAc/Hex)
  5. customto give 240 mg (28.2%) as colorless oil

Sources & evidence

ORD record
ord-34346d47025846879590cd775e8353ce
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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