Cesium carbonate → HCID 72550880, compound

HRID 590525Notes

Reaction equation

[NH2:1][C:2]1[N:3]([CH3:17])[C:4](=[O:16])[C:5]2([C:14]3[CH:13]=[C:12](Br)[S:11][C:10]=3[CH2:9][CH2:8][CH2:7]2)[N:6]=1.[C:18]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)#[N:19].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.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]>[NH2:1][C:2]1[N:3]([CH3:17])[C:4](=[O:16])[C:5]2([C:14]3[CH:13]=[C:12]([C:24]4[CH:25]=[C:20]([CH:21]=[CH:22][CH:23]=4)[C:18]#[N:19])[S:11][C:10]=3[CH2:9][CH2:8][CH2:7]2)[N:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

2′-amino-2-bromo-1′-methyl-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4′-imidazol]-5′(1′H)-one (0.127 g, 0.4 mmol), 3-cyanophenyl boronic acid (59 mg, 0.4 mmol) and Pd(dppf)Cl2 (33 mg, 0.04 mmol), were suspended in DMF (1.5 mL). Cs2CO3 (0.35 mL, 3.7 M aq. solution, 1.29 mmol) was added and the solution was degassed under a stream of nitrogen for 10 min. The mixture was heated at 90° C. for 2 hr. The reaction was cooled and solvent was removed in vacuo. The crude residue was purified using preparative HPLC to give the title compound as off-white solid (14 mg, 11%). 1H NMR δ (ppm)(DMSO-d6): 8.11 (1H, s), 7.86 (1H, d, J=8.18 Hz), 7.71 (1H, d, J=7.72 Hz), 7.57 (1H, t, J=7.85 Hz), 7.14 (1H, s), 6.41 (2H, br s), 3.02 (3H, s), 2.84-2.76 (2H, m), 2.11 (1H, d, J=13.56 Hz), 1.91 (2H, s), 1.70 (1H, s). HPLC (Method c) Rt 9.2 (min) m/z 337 (MH+).

Workup

customthe solution was degassed under a stream of nitrogen for 10 min
temperatureThe reaction was cooled
customsolvent was removed in vacuo
customThe crude residue was purified

Sources & evidence

ORD record: ord-8128678a8cb54488aa8c56d94609967e
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233982B2

Reaction notes

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