Cyanogen Bromide → 5-(8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-4-(2-chlorophenyl)-4H-1,2,4-triazol-3-amine

HRID 2078942Notes

Reaction equation

HRID 2078942 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15](=[N:24][NH2:25])[NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[Cl:23])=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:26]=1.[N:27]#[C:28]Br>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15]4[N:16]([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=5[Cl:23])[C:28]([NH2:27])=[N:25][N:24]=4)=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:26]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 178514378HCID 178514378, compound

Product 1

HCID 579002025-(8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-4-(2-chlorophenyl)-4H-1,2,4-triazol-3-amineYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
45 °C

Procedure

A solution of crude 8-bromo-N-(2-chlorophenyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbohydrazonamide (195, 0.434) in methanol (5 mL) was treated with a solution of cyanogen bromide (115 mg, 1.1 mmol) in methanol (1 mL) at room temperature. The reaction vessel was sealed and heated at 45° C. for 2 h, cooled to room temperature, quenched upon addition of saturated sodium bicarbonate and extracted with ethylacetate. The combined organics were dried over sodium sulfate and concentrated and the residue purified by flash column chromatography (1-10% MeOH in methylene chloride to give 287 (43 mg, 21% yield). MS (ESI): 475.0

Workup

  1. customThe reaction vessel was sealed
  2. temperaturecooled to room temperature
  3. customquenched upon addition of saturated sodium bicarbonate
  4. extractionextracted with ethylacetate
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. concentrationconcentrated
  7. customthe residue purified by flash column chromatography (1-10% MeOH in methylene chloride

Sources & evidence

ORD record
ord-8a78d7718d9a4c4699f934a38316c69c
Source dataset
uspto-grants-2011_04
Patent number
US07928248B2

Reaction notes

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