Sodium Carbonate → 2-[2-(1-Tritylpyrazolo[5,4-b]pyridin-4-yl)thiazol-4-yl]acetonitrile

HRID 44669Notes

Reaction equation

Br[C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]#[N:9])[N:6]=1.CC1(C)C(C)(C)OB([C:18]2[CH:23]=[CH:22][N:21]=[C:20]3[N:24]([C:27]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:25]=[CH:26][C:19]=23)O1.C([O-])([O-])=O.[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.CCOC(C)=O>[C:27]([N:24]1[C:20]2=[N:21][CH:22]=[CH:23][C:18]([C:2]3[S:3][CH:4]=[C:5]([CH2:7][C:8]#[N:9])[N:6]=3)=[C:19]2[CH:26]=[N:25]1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-(2-bromothiazol-4-yl)acetonitrile (575 mg, 2.832 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-pyrazolo[3,4-b]pyridine (1.840 g, 3.398 mmol), Na2CO3 (4.248 mL of 2 M, 8.496 mmol) and tetrakis(triphenylphosphine) Palladium(0) (130.9 mg, 0.1133 mmol) was heated in the microwave at 150° C. for 20 minutes. The reaction mixture was treated with water/EtOAc and extracted twice. The organics were dried (MgSO4), filtered, concentrated and purified (1:1 Petroleum ether/EtOAc,). The mixture was recolumned (Petroleum ether) to give the desired pure product (827 mg, 60% Yield). 1H NMR (CDCl3, 400 MHz) δ 4.04 (2H, s), 7.47 (2H, m), 8.34 (1H, m), 8.75 (1H, m); MS (ES+) 484.12

Workup

extractionextracted twice
dry with materialThe organics were dried (MgSO4)
filtrationfiltered
concentrationconcentrated
custompurified (1:1 Petroleum ether/EtOAc,)

Sources & evidence

ORD record: ord-38c637b906224091b2d62fe57e10374d
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541445B2

Reaction notes

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