Sodium Carbonate → HCID 50899241, compound

HRID 390110Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]2[C:8]([C:20]3[CH:25]=[C:24]([Cl:26])[N:23]=[C:22]([NH:27][CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)[CH:21]=3)=[CH:9][N:10](S(C3C=CC=CC=3)(=O)=O)[C:5]2=[N:4][CH:3]=1.[C:34]1(B(O)O)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.COCCOC.O.CCO.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CO>[Cl:26][C:24]1[N:23]=[C:22]([NH:27][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2)[CH:21]=[C:20]([C:8]2[C:6]3[C:5](=[N:4][CH:3]=[C:2]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:7]=3)[NH:10][CH:9]=2)[CH:25]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of EXAMPLE 38A (40 mg, 0.073 mmol), phenylboronic acid (11 mg, 0.088 mmol) and dichlorobis(triphenylphosphine)palladium (II) (5 mg, 0.007 mmol) was suspended in a mixture of 7:3:2 DME/H2O/EtOH (3 mL). 0.073 mL of 2 M aqueous Na2CO3 solution was added, and the mixture was heated in a microwave reactor at 150° C. for 20 minutes. Methanol (2 mL) was then added. The slightly yellow solid material was collected by filtration, washed with methanol, water, methanol, and dried to give the title product. Yield: 24 mg (82%). MS (DCI/NH3) m/z 546, 548 (M+H)+, 1H NMR (400 MHz, DMSO-d6): 1.16-1.40 (m, 4H), 1.61-1.67 (m, 1H), 1.73-1.79 (m, 2H), 1.95-2.01 (m, 2H), 3.37-3.41 (m, 2H), 3.57-3.64 (m, 1H), 6.80 (d, J=7.93 Hz, 1H), 7.25 (s, 1H), 7.47 (t, J=7.32 Hz, 1H), 7.55 (t, J=7.48 Hz, 2H), 7.62 (s, 1H), 8.24 (d, J=7.02 Hz, 2H), 8.61 (s, 1H), 8.92 (s, 1H).

Workup

filtrationThe slightly yellow solid material was collected by filtration
washwashed with methanol, water, methanol
customdried

Sources & evidence

ORD record: ord-01d3ef38e5a046a08a837a2b33ed6e2c
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383624B2

Reaction notes

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