Boron tribromide → HCID 57962073, compound

HRID 541575Notes

Reaction equation

HRID 541575 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[N:11][C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([CH:32]=3)[CH2:19][CH2:20][C:21]3[CH:29]=[C:25]([NH:26][C:27]=1[N:28]=2)[CH:24]=[CH:23][C:22]=3[O:30]C.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[N:11][C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([CH:32]=3)[CH2:19][CH2:20][C:21]3[CH:29]=[C:25]([NH:26][C:27]=1[N:28]=2)[CH:24]=[CH:23][C:22]=3[OH:30]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 66896681HCID 66896681, compound

Product 1

HCID 57962073HCID 57962073, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6-chloro-12-methoxy-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaene trifluoroacetate (157 mg, 0.34 mmol) in methylene chloride (2.5 mL) was cooled to −78° C. and 1 M boron tribromide in methylene chloride (1.68 mL, 1.68 mmol) was added slowly. The mixture was allowed to warm to room temperature and stir for 16 hours. The mixture was cooled to −78° C. and saturated sodium bicarbonate solution was added. The resulting suspension was filtered and the collected solid was washed with water and ethyl acetate to give the desired compound (113 mg, 100%). 1H NMR (300 MHz, DMSO-d6): δ 9.45 (s, 1H), 9.25 (s, 1H), 8.09 (s, 1H), 7.92 (s, 1H), 7.48 (s, 1H), 7.08 (m, 1H), 6.81 (m, 3H), 6.71 (d, 1H), 2.82 (s, 4H). LCMS for C18H16ClN4O (M+H)+: m/z=339.1.

Workup

  1. temperatureThe mixture was cooled to −78° C.
  2. filtrationThe resulting suspension was filtered
  3. washthe collected solid was washed with water and ethyl acetate

Sources & evidence

ORD record
ord-38d64b986d16478ea66d9c6758fa3bac
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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