Phenylboronic Acid → HCID 68638614, compound

HRID 2234108Notes

Reaction equation

I[C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:18]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[N:21]=[N:20][C:19]=1[O:30][CH3:31].[C:32]1(B(O)O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1(C)C=CC=CC=1.O.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>[CH3:31][O:30][C:19]1[N:20]=[N:21][C:22]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)=[CH:23][C:18]=1[C:3]1[NH:4][C:5]2[C:10]([C:2]=1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[CH:9][CH:8]=[C:7]([CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH:6]=2

Participants

Conditions

Temperature: 90 °C

Procedure

68 mg 3-Iodo-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-6-piperidin-1-ylmethyl-1H-indole, 17 mg phenylboronic acid, 86 mg potassium phosphate tribasic n-hydrate, and 12 mg tetrakis(triphenylphosphine)palladium(0) are dissolved in a mixture of 2.0 mL toluene and 72 μL water. Argon is bubbled through the solution for 5 minutes. The mixture is heated to 90° C. for 2.5 hours. Concentration in vacuo affords 62 mg crude product.

Workup

customArgon is bubbled through the solution for 5 minutes
concentrationConcentration in vacuo

Sources & evidence

ORD record: ord-b8bb718c5bd64ada862bcdf5c868a2eb
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709466B2

Reaction notes

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