Boron Trichloride → HCID 60104736, compound

HRID 1245496Notes

Reaction equation

HRID 1245496 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([Cl:42])[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([C@@H:12]3[O:32][C@H:31]([CH2:33][O:34]CC4C=CC=CC=4)[C@@H:22]([O:23]CC4C=CC=CC=4)[C@@H:13]3[O:14]CC3C=CC=CC=3)[C:6]=2[N:7]=1.B(Cl)(Cl)Cl>ClCCl>[NH2:1][C:2]1[N:3]=[C:4]([Cl:42])[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([C@@H:12]3[O:32][C@H:31]([CH2:33][OH:34])[C@@H:22]([OH:23])[C@@H:13]3[OH:14])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 86586074HCID 86586074, compound

Product 1

HCID 60104736HCID 60104736, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a precooled (−78° C.) solution of the compound from Step A (0.99 g, 1.7 mmol) in dichloromethane (30 mL) was added borontrichloride (1M in dichloromethane) (17 mL, 17.0 mmol) over a 10 min. The resulting solution was stirred at −78° C. for 1 h, allowed to warm to −15° C. and stirred for another 3 h. The reaction was quenched by addition of methanol/dichloromethane (1:1) (15 mL), stirred at −15° C. for 30 min, and pH adjusted to 7.0 by addtion of NH4OH. The mixture was evaporated in vacuo and the resulting oil purified on silica using methanol/dichloromehane (1:9) as eluent. Fractions containing the product were pooled and evaporated in vacuo to give the desired product (257 mg) as a colorless foam.

Workup

  1. temperatureto warm to −15° C.
  2. stirringstirred for another 3 h
  3. customThe reaction was quenched by addition of methanol/dichloromethane (1:1) (15 mL)
  4. stirringstirred at −15° C. for 30 min
  5. customThe mixture was evaporated in vacuo
  6. customthe resulting oil purified on silica
  7. additionFractions containing the product
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-7fd52de279124bd88410c83a6748f428
Source dataset
uspto-grants-2006_10
Patent number
US07125855B2

Reaction notes

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