Boron Trichloride → HCID 54689907, compound

HRID 1244128Notes

Reaction equation

HRID 1244128 reaction equation
B(Cl)(Cl)Cl.C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[C:23]3[C:22]([OH:24])=[C:21]([C:25]#[N:26])[C:20](=[O:27])[NH:19][C:18]=3[S:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)C=C>ClCCl>[OH:24][C:22]1[C:23]2[C:15]([C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=3)=[CH:16][S:17][C:18]=2[NH:19][C:20](=[O:27])[C:21]=1[C:25]#[N:26]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 54689901HCID 54689901, compound

Product 1

HCID 54689907HCID 54689907, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trichloride (1M in dichloromethane, 5 mL, 5 mmol) was added to a solution of 3-[3-(allyloxy)phenyl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (146B) (0.54 g, 1.65 mmol) in dichloromethane (30 mL) and the reaction was stirred at room temperature for 16 h. It was quenched with water (20 mL), filtered, concentrated and purified on a RP-HPLC system. The title compound was one of the three reaction products that were purified. MS (ESI) m/e 283.0 (M−H)+; 1H NMR (500 MHz, DMSO-d6): δ ppm 12.46 (br s, 1H), 9.36 (br s, 1H), 7.14 (t, 1H), 6.96 (s, 1H), 6.83–6.80 (m, 2H), 6.7–6.72 (m, 1H).

Workup

  1. customIt was quenched with water (20 mL)
  2. filtrationfiltered
  3. concentrationconcentrated
  4. custompurified on a RP-HPLC system
  5. customone of the three reaction products that
  6. customwere purified

Sources & evidence

ORD record
ord-0b1c967bc79b4494bf28028069823592
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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