Cesium carbonate → HCID 59548534, compound

HRID 1879683Notes

Reaction equation

HRID 1879683 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:3]=1[CH:4]=[O:5].[CH:11]1([C:14]2[CH:15]=[CH:16][C:17]3[C:23](=[O:24])[NH:22][CH2:21][CH2:20][NH:19][C:18]=3[CH:25]=2)[CH2:13][CH2:12]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[Br:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([N:22]2[C:23](=[O:24])[C:17]3[CH:16]=[CH:15][C:14]([CH:11]4[CH2:13][CH2:12]4)=[CH:25][C:18]=3[NH:19][CH2:20][CH2:21]2)[C:3]=1[CH:4]=[O:5]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 126486412,6-DibromobenzaldehydeHCID 59548528HCID 59548528, compound

Product 1

HCID 59548534HCID 59548534, compoundYield 88.3%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2,6-Dibromo-benzaldehyde (1.06 g, 4 mmol, 4 eq), 8-Cyclopropyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (202 mg, 1 mmol, 1 eq), Xantphos (12 mg, 0.02 mmol, 0.02 eq), Pd(dba)2 (18 mg, 0.03 mmol, 0.03 eq), cesium carbonate (652 mg, 2 mmol, 2 eq.) in 40 mL dioxane was degassed with argon for 1 min, and heated to 100 C for 14 hours under an argon atmosphere. The reaction was cooled, and the filtered through a sintered glass funnel, concentrated to dryness and triturated with CH2Cl2. The filtrated was purified on a silica gel column using a gradient of 30 to 40% ethyl acetate in hexanes to give 340 mg 2-Bromo-6-(8-cyclopropyl-5-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-benzaldehyde, 88% which was suitable for use in the next step.

Workup

  1. customwas degassed with argon for 1 min
  2. temperatureheated to 100 C for 14 hours under an argon atmosphere
  3. temperatureThe reaction was cooled
  4. filtrationthe filtered through a sintered glass funnel
  5. concentrationconcentrated to dryness
  6. customtriturated with CH2Cl2
  7. customThe filtrated was purified on a silica gel column

Sources & evidence

ORD record
ord-cccebc10120c4bf1864897b03cff40a5
Source dataset
uspto-grants-2012_11
Patent number
US08318719B2

Reaction notes

Loading…