Dichloromethane → HCID 86700922, compound

HRID 1424380Notes

Reaction equation

HRID 1424380 reaction equation
C([O:8][C:9]1[C:14]2[CH:15]=[C:16]([C:18]3[N:19]=[C:20]4[N:24]([CH:25]=3)[N:23]=[C:22]([C@@H:26]([F:28])[CH3:27])[S:21]4)[O:17][C:13]=2[CH:12]=[C:11]([O:29][CH3:30])[CH:10]=1)C1C=CC=CC=1.CC1C(C)=C(C)C(C)=C(C)C=1.ClCCl.B(Cl)(Cl)Cl>>[F:28][C@H:26]([C:22]1[S:21][C:20]2=[N:19][C:18]([C:16]3[O:17][C:13]4[C:14](=[C:9]([OH:8])[CH:10]=[C:11]([O:29][CH3:30])[CH:12]=4)[CH:15]=3)=[CH:25][N:24]2[N:23]=1)[CH3:27]

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 12784PentamethylbenzeneHCID 25135Boron TrichlorideHCID 86700920HCID 86700920, compound

Product 1

HCID 86700922HCID 86700922, compound

Conditions

Temperature
-78 °C

Procedure

A mixture of (S)-6-(4-(benzyloxy)-6-methoxybenzofuran-2-yl)-2-(1-fluoroethyl)imidazo[2,1-b][1,3,4]thiadiazole (Example 40B, 0.152 g, 0.359 mmol) and pentamethylbenzene (0.374 g, 2.52 mmol) in dichloromethane (24 ml, 373 mmol) was cooled to −78° C. under nitrogen atmosphere and then treated immediately (to avoid crystallization) with boron trichloride 1.0M in dichloromethane (1 ml, 1.000 mmol) added dropwise over 3 min. The resulting mixture was stirred at −78° C. for 1 h. The reaction mixture was quenched by addition of a solution of sodium bicarbonate (0.71 g) in water (12 mL) added in one portion. The cooling bath was removed and the resulting mixture was stirred at room temperature for 1 h. The solid formed was filtered, washed successively with water (8 mL) and dichloromethane (8 mL). The filter cake was soaked with anh. ethanol and suck dried. The white solid obtained was dried under vacuum on P2O5 for 36 h. LC (Method B): 2.038 min. MS (ESI) calcd. for C15H13FN3O3S [M+H]+ m/z: 334.0656. found: 334.0680. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.06 (s, 1H) 8.56 (s, 1H) 7.09 (s, 1H) 6.67 (s, 1H) 6.26-6.28 (m, 1H) 6.16 (dq, J=46.9, 6.4 Hz, 1H) 3.76 (s, 3H) 1.80 (dd, J=24.7, 6.3 Hz, 3H).

Workup

  1. additiontreated immediately
  2. additionadded dropwise over 3 min
  3. customThe reaction mixture was quenched by addition of a solution of sodium bicarbonate (0.71 g) in water (12 mL)
  4. additionadded in one portion
  5. customThe cooling bath was removed
  6. stirringthe resulting mixture was stirred at room temperature for 1 h
  7. customThe solid formed
  8. filtrationwas filtered
  9. washwashed successively with water (8 mL) and dichloromethane (8 mL)
  10. customdried
  11. customThe white solid obtained
  12. customwas dried under vacuum on P2O5 for 36 h
  13. custom2.038 min

Sources & evidence

ORD record
ord-2cc807ff36854139a1e9c09ae952c8aa
Source dataset
uspto-grants-2015_01
Patent number
US08927688B2

Reaction notes

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