Potassium Phosphate, Tribasic → HCID 68155810, compound

HRID 1877807Notes

Reaction equation

HRID 1877807 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:10]([CH:11]=1)[CH2:9][C:8]1[CH:12]=[C:13]([CH3:16])[CH:14]=[CH:15][C:7]=1[N:6]=[C:5]2[N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]([CH3:30])([CH3:29])[C:25]([O:27][CH3:28])=[O:26])[CH2:19][CH2:18]1.N1C=CC=[CH:33][CH:32]=1.C(B1OB(C=C)OB(C=C)O1)=C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CO.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2]>[CH2:32]([C:2]1[CH:3]=[C:4]2[N:10]([CH:11]=1)[CH2:9][C:8]1[CH:12]=[C:13]([CH3:16])[CH:14]=[CH:15][C:7]=1[N:6]=[C:5]2[N:17]1[CH2:18][CH2:19][N:20]([CH2:23][C:24]([CH3:30])([CH3:29])[C:25]([O:27][CH3:28])=[O:26])[CH2:21][CH2:22]1)[CH3:33]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27348062,4,6-Trivinylboroxin-Pyridine ComplexHCID 68156188HCID 68156188, compound

Product 1

HCID 68155810HCID 68155810, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 12976736Bis(ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane);iron(2+)CatalystHCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

Mix methyl 3-[4-(2-bromo-7-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoate (1.00 equiv; 620.00 mg, 1.31 mmoles), triethenylboroxin pyridine (1.5 equiv; 472.79 mg, 1.96 mmoles;) in methanol (15 mL). Add a pre-blended mixture of 1.09 wt % tris(dibenzylideneacetonyl)bis-palladium (Pd2(dba)3), 1.16 wt % 1,1′-bis(di-tert-butylphosphino)ferrocene (dtbpf) and 97.75 wt % tripotassium phosphate (1.10 g) and heat at 140° C. for 25 mins in a microwave. Filter the reaction mixture through celite and dilute to 25 mL volume with methanol. Hydrogenate the methanolic solution by passing at 1 mL/min. through a H-Cube® flow hydrogenator using a 10% Pd/C catalytic cartridge at 50° C. Evaporate the solvent in vacuo to give methyl 3-[4-(2-ethyl-7-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoate. MS (m/z): 423.18 (M+1).

Workup

  1. additionAdd
  2. filtrationFilter the reaction mixture through celite
  3. additiondilute to 25 mL volume with methanol
  4. customat 50° C
  5. customEvaporate the solvent in vacuo

Sources & evidence

ORD record
ord-d548251aa95c40eaa07caf0178dd75fd
Source dataset
uspto-grants-2012_11
Patent number
US08314092B2

Reaction notes

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