Phenylboronic Acid → HCID 10194764, compound

HRID 2415628Notes

Reaction equation

HRID 2415628 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][CH:9]2[CH2:14][CH2:13][CH:12]([NH:15][C:16]3[C:25]4[C:20](=[CH:21][C:22]([Cl:26])=[CH:23][CH:24]=4)[N:19]=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)[CH:5]=[N:6][CH:7]=1.C[O-].[Na+].[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:26][C:22]1[CH:21]=[C:20]2[C:25]([C:16]([NH:15][CH:12]3[CH2:13][CH2:14][CH:9]([NH:8][C:4]4[CH:5]=[N:6][CH:7]=[C:2]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[CH:3]=4)[CH2:10][CH2:11]3)=[CH:17][CH:18]=[N:19]2)=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 66827Phenylboronic AcidHCID 10216670HCID 10216670, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 10194764HCID 10194764, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of example 370 (30 mg, 0.07 mmol), Pd(dppf)Cl2 (3 mg), sodium methoxide (7.5 mg, 0.14 mmol) and phenylboronic acid (9.7 mg, 0.07 mmol) in 1 ml THF was heated for 15 Hours at 65° C., concentrated. Residue was purified with high throughput reverse phase HPLC system to provide the desired compound. MS (ESI(+)Q1MS m/z 429 (M+H)+); 1 H NMR (300 MHz, DMSO-D6) δ ppm 1.75-2.01 (m, 8 H) 3.84 (m, 1 H) 4.04 (m, 1 H) 7.52-7.60 (m, 3 H) 7.74-7.84 (m, 4 H) 7.94 (d, J=2.03 Hz, 1 H) 8.13 (d, J=2.37 Hz, 1 H) 8.33 (s, 1 H) 8.58 (d, J=7.12 Hz, 1 H) 8.73 (d, J=9.15 Hz, 1 H) 8.94 (d, J=6.78 Hz, 1 H).

Workup

  1. concentrationconcentrated
  2. customResidue was purified with high throughput reverse phase HPLC system

Sources & evidence

ORD record
ord-6b7e2c97167a4429bbe2f9d289a0e372
Source dataset
uspto-grants-2004_11
Patent number
US06818772B2

Reaction notes

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