Potassium Phosphate, Tribasic → HCID 57763140, compound

HRID 230763Notes

Reaction equation

HRID 230763 reaction equation
I[C:2]1[C:6]2[CH:7]=[N:8][C:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:10][C:5]=2[N:4](C(OCC)=O)[CH:3]=1.[N+:23]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)([O-:25])=[O:24].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:23]([C:26]1[CH:31]=[CH:30][C:29]([C:2]2[C:6]3[CH:7]=[N:8][C:9]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])=[CH:10][C:5]=3[NH:4][CH:3]=2)=[CH:28][CH:27]=1)([O-:25])=[O:24]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27735524-Nitrophenylboronic acidHCID 57763149HCID 57763149, compound

Product 1

HCID 57763140HCID 57763140, compoundYield 18.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
77.5 °C

Procedure

To a mixture of 6-tert-butyl 1-ethyl 3-iodo-1H-pyrrolo[3,2-c]pyridine-1,6-dicarboxylate (55 mg, 0.13 mmol) and 4-nitrophenylboronic acid (67 mg, 0.4 mmol) in toluene (3 mL) and ethanol (1.5 mL), was added Pd(PPh3)4, followed by K3PO4 (2 M, 0.4 mL). The resulting mixture was purged with argon, and heated at 75-80° C. for 5 h. The desired product was purified by prep-HPLC to gave a yellow solid (8 mg, 18 % yield). 1H NMR (CDCl3) δ 8.68 (s, 1H), 8.30 (d, 2H, J=8.8 Hz), 8.00 (d, 1H, J=8.8 Hz), 7.36 (s, 1H), 7.25 (s, 1H), 1.51 (s,9H) ; LC-MS: m/z 284 (M-Bu)+.

Workup

  1. customThe resulting mixture was purged with argon
  2. customThe desired product was purified by prep-HPLC

Sources & evidence

ORD record
ord-9392d7162c36425e8e2fb7c1c701295a
Source dataset
uspto-grants-2009_07
Patent number
US07566784B2

Reaction notes

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